Diisopropylethylamine → HCID 59003319, compound

HRID 2267594Notes

Reaction equation

[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[S:34]1[CH:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35]1>C(Cl)(Cl)Cl>[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[C:14]([C:16]([NH2:18])=[O:17])[CH:15]=2)[NH:12][CH:11]=[C:10]3[CH:19]2[CH2:24][CH2:23][N:22]([S:39]([C:36]3[CH:37]=[CH:38][S:34][CH:35]=3)(=[O:41])=[O:40])[CH2:21][CH2:20]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 5-Phenyl-3-(4-piperidinyl)-1H-indole-7-carboxamide (31 mg/0.067 mmol) in CHCl3 (1.0 ml) was added diisopropyl ethylamine (3 eq). The mixture was cooled to −10° C. and then added to 3-thiophenesulfonyl chloride. The solution was agitated for 1.5 h. Solid phase extraction (SPE) using an aminopropyl cartridge (500 mg) and elution with CHCl3 followed by ethyl acetate provided the title compound (19 mg 61%). LC/MS: m/z 465 Rt 2.29 min.

Workup

extractionSolid phase extraction (SPE)
washan aminopropyl cartridge (500 mg) and elution with CHCl3

Sources & evidence

ORD record: ord-f8ba1446a38a44f79f049d9d28597b72
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07858796B2

Reaction notes

Loading…